17277-58-6

Usage

Uses

Used in Cosmetic and Fragrance Industry:
METHYL (PHENYLTHIO)ACETATE is used as a fragrance ingredient for its strong aroma and pleasant, fruity scent. It is a valuable component in the production of perfumes, soaps, and lotions, enhancing their overall fragrance profile.
Used in Food Industry:
METHYL (PHENYLTHIO)ACETATE is used as a flavoring agent, particularly in the production of confectionery and baked goods. Its fruity aroma adds a desirable taste and aroma to these food products.
However, individuals with sensitivity to fragrances may experience adverse reactions to products containing METHYL (PHENYLTHIO)ACETATE. Therefore, caution should be exercised when using products that contain this chemical, and consumers should be made aware of its presence in the ingredients list.

InChI:InChI=1/C9H10O2S/c1-11-9(10)7-12-8-5-3-2-4-6-8/h2-6H,7H2,1H3

Upstream product

• 67-56-1 methanol 
• 103-04-8 (phenylthio)acetic acid 
• 591-50-4 iodobenzene 
• 76310-90-2 Methoxycarbonylmethylthiotrimethylstannane 
• 14090-83-6 methyl 2-phenylsulfinylacetate 
• 930-69-8 sodium thiophenolate 
• 96-34-4 methyl chloroacetate 
• 108-98-5 thiophenol 
• 2483-57-0 methyl 2-nitroacetate 
• 186581-53-3 diazomethane 
• 79-11-8 chloroacetic acid 
• 36850-80-3 [(1-methoxyvinyl)oxy]trimethylsilane 
• 194720-38-2 2,3,5,6-tetramethyl-4-oxo-1-phenylthiocyclohexa-2,5-dienyl 2-chloroacetate 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 13865-02-6 methoxyphenylsulfanylacetic acid methyl ester 
• 63787-29-1 [4-(2-Chloro-acetyl)-phenylsulfanyl]-acetic acid methyl ester 
• 121671-51-0 (E)-(2R,3S)-3-Hydroxy-5-phenyl-2-phenylsulfanyl-pent-4-enoic acid methyl ester 
• 121671-51-0 (E)-(2R,3R)-3-Hydroxy-5-phenyl-2-phenylsulfanyl-pent-4-enoic acid methyl ester 
• 121671-43-0 (2R,3S)-3-Hydroxy-5-phenyl-2-phenylsulfanyl-pentanoic acid methyl ester 
• 121671-43-0 (2R,3R)-3-Hydroxy-5-phenyl-2-phenylsulfanyl-pentanoic acid methyl ester 
• 13307-60-3 2-methyl-1-(phenylthio)propan-2-ol 
• 84796-82-7 methyl 4-oxo-2-(phenylthio)pentanoate 
• 125442-81-1 (3-Oxo-cyclohexyl)-phenylsulfanyl-acetic acid methyl ester 
• 74143-92-3 (E)-methyl 5,9-dimethyl-2-(phenylthio)-4,8-decadienoate 
• 125442-80-0 (3-Oxo-cyclopentyl)-phenylsulfanyl-acetic acid methyl ester 
• 5042-53-5 1-(phenylsulfanyl)acetone 
• 100-68-5 methyl-phenyl-thioether 
• 127223-15-8 1-(2-Phenylthioethyl)cyclopropanol 

Relevant academic research and scientific papers

Scalable electrochemical reduction of sulfoxides to sulfides

A scalable reduction of sulfoxides to sulfides in a sustainable way remains an unmet challenge. This report discloses an electrochemical reduction of sulfoxides on a large scale (>10 g) under mild reaction conditions. Sulfoxides are activated using a substoichiometric amount of the Lewis acid AlCl3, which could be regeneratedviaa combination of inexpensive aluminum anode with chloride anion. This deoxygenation process features a broad substrate scope, including acid-labile substrates and drug molecules.

Photocatalytic Deoxygenation of Sulfoxides Using Visible Light: Mechanistic Investigations and Synthetic Applications

The photocatalytic deoxygenation of sulfoxides to generate sulfides facilitated by either Ir[(dF(CF3)ppy)2(dtbbpy)]PF6 or fac-Ir(ppy)3 is reported. Mechanistic studies indicate that a radical chain mechanism operates, which proceeds via a phosphoranyl radical generated from a radical/polar crossover process. Initiation of the radical chain was found to proceed via two opposing photocatalytic quenching mechanisms, offering complementary reactivity. The mild nature of the radical deoxygenation process enables the reduction of a wide range of functionalized sulfoxides, including those containing acid-sensitive groups, in typically high isolated yields.

Rhodium-catalyzed Sommelet-Hauser type rearrangement of α-diazoimines: Synthesis of functionalized enamides

An efficient rhodium catalyzed Sommelet-Hauser type rearrangement of sulfur ylides derived from α-thioesters and N-sulfonyl-1,2,3-triazoles has been successfully accomplished for the synthesis of various functionalized enamides. The developed reaction involves the unprecedented [2,3]-sigmatropic rearrangement of sulfur ylides with the imine motif. Importantly, the method works well with various substituted α-thioesters/-amides/-ketones and substituted N-sulfonyl-1,2,3-triazoles and allows the synthesis of diverse enamide derivatives in good to excellent yields. The reaction was also successfully extended to the one-pot synthesis of enamides from terminal alkynes.

Compound, preparation method thereof, medical intermediate and application thereof

The invention relates to the technical field of chemical synthesis, and particularly discloses a compound, a preparation method thereof, a medical intermediate and an application thereof, the compoundcomprises the following raw materials: thioether, bromide and a proper amount of organic solvent, and the molar weight ratio of thioether to bromide is 1: (2-8). According to the compound provided bythe invention, thioether, bromide and a proper amount of organic solvent are used as raw materials, and the thioether compound can be obtained without adopting a catalyst, so that the problems of metal residues and the like are fundamentally eliminated, the provided preparation method is simple to operate, the method is simple in process and high in yield, the thioether compound is prepared through thioether metathesis reaction, metal catalysis is not needed in the whole reaction, meanwhile, the reaction condition is mild, the substrate range is wide, the problem of metal pollution existing in an existing thioether compound synthesis method is solved, and the method has wide market prospects in the fields of organic synthesis, medicine synthesis and the like.

Sulfoxide Reduction/C(sp3)-S Metathesis Cascade in Ionic Liquid

A sulfoxide reduction/C-S bond metathesis cascade between sulfoxides and alkyl bromides has been developed to access high-value sulfides without the use of any catalysts or bases. In this cascade, classical Kornblum oxidation is employed to reduce sulfoxides with alkyl bromides in ionic liquid. This protocol features high functional tolerance, mild conditions, promising scalability, and sustainable solvents.

A Manganese N-Heterocyclic Carbene Catalyst for Reduction of Sulfoxides with Silanes

The first reduction of sulfoxides catalysed by a well-defined manganese complex is described. A variety of sulfoxides are reduced to the corresponding sulfides in high yields using phenylsilane, diphenylsilane, and the economically feasible 1,1,3,3-tetramethyldisiloxane (TMDS) as reducing agents in the presence of a Mn-NHC complex. The reaction is performed under air and without the need of any additive. The involvement of radicals in the catalytic reaction is probed by spin-trap experiments.

Gold-Catalyzed Oxidation of Thioalkynes to Form Phenylthio Ketene Derivatives via a Noncarbene Route

Gold-catalyzed oxidations of thioalkynes with 8-methylquinoline oxides afford 2-phenylthioketenes that can be trapped efficiently with alcohols. The synthetic utility is manifested by terminal and internal thioalkynes over a wide scope, bearing esters, ke

Dealkylative intercepted rearrangement reactions of sulfur ylides

Sulfur ylides are well-known to undergo sigmatropic rearrangement reaction. Herein, we describe a novel reactivity of sulfur ylides, which provides access to the product of a formal functional group metathesis upon dealkylative interception of the rearrangement process. Using a simple iron catalyst and in situ generated diazoalkanes this method provides access to α-mercaptoacetonitrile derivatives.

Rhodium-Catalyzed Rearrangement of S/Se-Ylides for the Synthesis of Substituted Vinylogous Carbonates

An efficient rhodium-catalyzed unprecedented oxa-[2,3]-sigmatropic rearrangement of sulfur ylide derived from α-thioesters/ketones and diazo carbonyl compounds has been accomplished for the synthesis of various sulfur-tethered vinylogous carbonates in good to excellent yields. Important features of the developed reaction include wide functional group tolerance, excellent chemo- and regioselectivity, and efficient rearrangement involving the carbonyl motif. The present reaction also equally works well with α-selenoesters for the synthesis of seleno-containing vinylogous carbonates.

Synthesis and computer-aided SAR studies for derivatives of phenoxyalkyl-1,3,5-triazine as the new potent ligands for serotonin receptors 5-HT6

This research has provided the most active 5-HT6R agents among 1,3,5-triazine derivatives investigated to date and has also identified the world's first selenium-containing 5-HT6R ligands. The studies are focused on design, synthesis, biological evaluation and docking-supported SAR analysis for novel 5-HT6R agents as derivatives of lead structure 4-(4-methylpiperazin-1-yl)-6-(phenoxymethyl)-1,3,5-triazin-2-amine (7). The lead modifications included an introduction of: (i) various small substituents at benzene ring, (ii) a branched ether linker or (iii) the ether oxygen replacement with other chalcogen (S, Se) or sulfonyl moiety. Hence, a series of new compounds (7–24) was synthesized and examined on their affinities for 5-HT6R and selectivity, in respect to the 5-HT1AR, 5-HT2AR, 5-HT7R and dopamine D2 receptor, in the radioligand binding assays. For representative most active compounds functional bioassays and toxicity profile in vitro and antidepressant-like activity in vivo were examined. The 2-isopropyl-5-methylphenyl derivative (10) was found as the most active triazine 5-HT6R antagonist (Ki = 11 nM). SAR analysis indicated, that an exchange of oxygen to selenium (7 vs. 22), and especially, to sulfur (7 vs. 19) was beneficial to increase both affinity and antagonistic action for 5-HT6R. Surprisingly, an introduction of SO2 caused a drastic decrease of the 5-HT6R affinity, which was explained at a molecular level based on docking studies. All in vivo tested compounds (10, 18 and 21) did not show any risk of toxicity in the safety studies in vitro.